The Perfect Three-Day Weekend in Pittsburgh

Here’s what to do on a long weekend in Pittsburgh.

The Perfect Three Days in Pittsburgh
Photo: UIG via Getty Images

Pennsylvania’s second-largest city has always been fiercely loved by its locals. Now, word of Pittsburgh’s gritty-meets-quirky charm is spreading. Without some guidance, it can be hard to blend the classic must-stops with the latest crop of hot-spot restaurants and still manage to toss in a few off-the-path finds, too. But not to worry, we mapped out all of that and more.

So, pack your comfy walking shoes for a few days of eating well, getting cultured, and crossing lots of bridges. Here’s what to do in Pittsburgh for the perfect three-day weekend.

Day One

If you’ve arrived at Pittsburgh International Airport, you’ll be heading into the city through the Fort Pitt Tunnel, so make sure you have your eyes peeled (away from your phone) for the first glimpse of the skyline on the other side. It’s a stunning welcome, one that never gets old, even for locals.

Check in at Kasa The Maverick, formerly the Ace Hotel, or Hotel Indigo in East Liberty, and if you’d rather stay in the area for the evening, walk down South Highland Avenue toward Shadyside, where you’ll likely pass Muddy Waters, an oyster bar with a Cajun-inspired menu, and Mola, a semi-casual sushi spot with cocktails and bubble tea.

If you’re keen on exploring more, take an Uber — about a 10-minute ride — over to Butler Street in Lawrenceville. Here you’ll find some of the best shopping in Pittsburgh; for ‘Burgh-themed gifts, clothes, and other oddities, don’t miss Wildcard, No. 14 Boutique, and the balloon store Von Walter & Funk. You could also take a trip to Coven Brewing, a recent arrival to the craft brew scene opened by two Dancing Gnome veterans.

When it’s time for dinner, you’re just a few blocks from two of the city’s best restaurants. Try The Vandal for casual, contemporary American, or Morcilla for Spanish-style charcuterie and traditional pintxos. Get your nightcap at Allegheny Wine Mixer for great wine in a kitschy, living room-like atmosphere or get your groove on into the midnight hours on the dance floors at Remedy or Spirit. Other great cocktail spots include Bar Botanico in Lawrenceville and Bridges & Bourbon in the Cultural District.

Day Two

There’s no better place to fuel up for an active day ahead than Pamela’s. Heading to the Strip District location around 8:30 or 9:00 a.m. will help you beat the incoming crowd also looking to get their forks on a plate of the diner’s famous crêpe-style hotcakes.

After you’ve cleaned up any stray drops of syrup, spend some time perusing the shops and Old World markets along Penn Avenue for locally crafted wares, gourmet treats, and every kind of Pittsburgh sports fan gear imaginable. Right next door to Pamela's, rent a bike at the POGOH station —  just $4 for every 30 minutes — and pedal toward the trail along the Allegheny River. This path will take you all the way downtown to Point State Park, where a fountain marks the intersection of the three rivers.

You’ll pass four bikeable bridges, and the trail across the river on the North Shore is beautiful, too. If you want to spend more time biking, the ride out to Washington’s Landing is one of the best — about 30 minutes out and back along the river.

Once you make it to the Point, stop for a photo op and a break at the fountain, and then head to Market Square to return your bike and check out downtown. For an early dinner in an Instagram-worthy interior, make a reservation at Tako or go for the wood-fired steak Argentina-style at Gaucho Parilla.

You’re in the perfect place to catch a show or check out a gallery in the Cultural District, but if you’re up for a more panoramic view, take the Wood Street T to Station Square and head up the Monongahela Incline train to watch the sunset above the skyline from the overlook on Mt. Washington. If you’re planning anything romantic for your trip, this is the place to do it.

From there, East Carson Street in the South Side — the main nightlife stretch in the city — is just a few minutes’ drive, and bars like The Urban Tap are sure to be lively until they close at 11 p.m. or later. If you’re thirsty for something a little (OK, a lot) sweeter, The Milk Shake Factory right down the street is open until 10 p.m.

Day Three

After a hearty brunch at Kelly O's Diner in the Hill District, take an Uber over to the North Side to spend a few hours with contemporary installation art at the Mattress Factory or the Pittsburgh-born Prince of Pop Art at the Andy Warhol Museum. If you have some extra time, spend it strolling the cobblestoned sidewalks of the historic Mexican War District.

And finally, your trip wouldn’t be complete without experiencing the Steel City’s notorious sports culture firsthand. If you can’t score seats at a Steelers game, Pirates tickets are usually pretty affordable for bleacher seats at the beautiful PNC Park. If you try a coleslaw-and-French-fry-piled sandwich from Primanti Brothers for dinner — there are locations at both stadiums—you just might reach peak Pittsburgh.

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